Road trip on Route 66: A legendary road and its stories.

Did you know that Route 66 starts right in the heart of Chicago? At The Bean around the corner, so to speak? A few days in Chicago can be perfectly combined with a short trip along Route 66: A real American road trip. Just like in the movie.

Route 66. The name alone evokes all sorts of associations: I dream of freedom, endless roads through the American Midwest, and driving, driving, driving into the vastness of a country that seems both more mysterious and more fascinating to me with every visit. Did you actually know that Route 66 starts right in the heart of Chicago? Just around the corner from The Bean, so to speak? This makes it perfect to combine a few days in Chicago with a short trip along Route 66: a truly American road trip! Just like in the movies. Itโ€™s always been on my โ€œmust-see-in-my-lifetimeโ€ list.

historic route sign

The charm of the Midwest

Starting in Chicago, you can follow the old Route 66 throughout Illinois, and it feels like traveling back in time through the America of the last century. Every place along Route 66 in Illinois has its own charm and its own history in connection with the road that criss-crossed not only the country but also people’s lives. And it was these that made this road trip so special.

old gas station on the route

Even in Chicago, I was struck by the incomparable friendliness of the people. The gruff Berliner in me was irritated when, on more than one occasion, complete strangers threw themselves in front of me just to hold the door open for me. Or spontaneous high-fives with shoe sellers who admired my shoes. Or strange women shouting at you in the middle of the street: “I love your skirt!” Just like that. Because you can say something nice out loud instead of just looking furtively. In general, being nice is a basic requirement for life here. And we were still in an anonymous city!

cornfield in illinois

But things got even more amazing when we left the city on our road trip. Chicago itself only has 2.7 million inhabitants, and the rest is so spread out that you quickly get the feeling that you’re in the countryside as soon as you leave the city by car.

Who’s blogging here?

Hey, I’m Tatiana & the blogger behind The Happy Jetlagger. I write honestly, passionately and authentically about my travels. All tips have been researched by myself!

on the historic route in illinois

And this is where the positive energy and joie de vivre of the Midwest really hits you. Not once, not a single damn time, did I have the feeling of encountering bad-tempered or unfriendly people on our road trip. It was crazy, almost unreal. On the contrary, the joy of showing his city, his Route 66, his Midwest, was a gesture from everyone’s heart – and this paragon of a positive attitude to life and pure, genuine joy was so infectious that for the first time I really understood why people are so fascinated by America.

Route 66 – a road full of American history

Actually, Route 66 no longer exists as an official road. At some point, no one was in the mood for almost 4,000 kilometers of cobblestones and/or single-lane country roads: Route 66 was put into operation as early as 1926 as the most important east-west connection.

โžœ You can find out more about Route 66 and what you can experience there here

old motel signs in illinois

What was a revolution for the infrastructure at the time was no longer sufficient to cope with the increasing traffic. Route 66 was relocated and rebuilt several times until it was replaced by interstate highways in most places. What remained was the legend. Along with the quirky stories, the warm-hearted people and the many rest stops and stores along the road that lured passing cars with the most eye-catching signs and craziest buildings.

cozy dog diner price list

*Transparency: I was invited on this trip by Enjoy Illinois for research purposes. for research purposes.


*Links marked with an asterisk (*) are affiliate links. If you book or buy something through them, I will receive a small commission. Thank you for your support!


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